1998: Lynn Tilton comes up with an idea for a Christmas card. It includes two wardrobe changes, several stuffed animals, a stool, a stepladder, a whip, a Santa hat, red leather cowboy boots, and black knee-high boots. She shoots it and sends it to her clients on Wall Street. It looks like this:

2015: Tilton tells Bloomberg BusinessWeek: “I had been working with very few accounts,” Tilton says. “They were all very close friends, and because most of sales is on the phone, I would get asked all the time, ‘What are you wearing today? What color is your underwear?’ And it didn’t offend me. It was part of the interaction of what I did.” She pauses for a calculated toss of her hair. She had saved a bunch of money, she says, and planned to retire. “My joke to them was, on my way out, I showed them the color of my underwear.” “My mother told me I would regret it,” she says, sighing. “And I hate when my mother is right.”